We were just over 16 years old when I and my childhood best friend Tim, discovered masturbation. And once we did, we couldn't have enough of it. More often than not we would be at secluded places jerking off over porn magazines. From then onwards I realised I was getting more excited watching Tim masturbating rather than the porn, and soon I started wondering rather intensively how would his cock feel in my hand and mouth. But I was always too scared to ask to touch or taste it. The curiosity soon turned into a desire that would occupy my mind even when on my own.
Tim's parents were divorced. He lived with his mum, his older brother Kevin who usually ignored us and his older sister Fen who was never at home. Tim and I grew up together, our mums were best friends and we would frequently spend the night at each other's place.
After one such night, I woke up in the spare bed at Tim's room, starring blurrily at Tim standing in front of his bed, sporting a huge bulge under his pyjamas. I was fully awake and horny on the spot. I got up shortly after he left the room and got ready for breakfast. At the table my eyes were continuously drawn at Tim's crotch. During one of those brief moments I thought I saw Kevin from the corner of my eye staring at me and smiling. It all lasted seconds and after seeing no further reaction from Kevin, I dismissed it as something I imagined.
Lost in my cock filled thoughts I barely noticed their mum inviting me to their grandmas and Kevin telling her I'd stay home with him and keep him company till they were back. Up until then, Kevin had acknowledged my presence only a handful of times and I was quite surprised at all the attention. Stunned for a few seconds, before I could say a word, they were already out of the room getting ready to go.
When they were gone I went to Tim's room, everything forgotten already, and started reading a book, trying to occupy myself.
'Hey George, do you wanna come over watch a film with me? I'm getting really bored on my own!' I heard Kevin shouting from the living room.
When I walked in, he was sitting on the couch wearing track suits and a t-shirt, and as I sat on the other couch I couldn't help but notice that he was sporting a huge hard-on under his pants. That's when I realised that he was watching porn on the TV.
'What, you've never watched porn before?' he said grinning at me as my face was becoming fast red.
'Of course I have!' I replied somewhat defiantly with a hint of pride in my voice.
'Great' he said still grinning at me, 'I thought you had.'
His last remark made my chest swell with pride. Kevin was treating me as an equal and I was determined to be cool and chilled.
'Come, sit next to me,' he said pointing by his side, 'you can see better from here'.
I sat next to him casually trying to act cool. As we were sitting there watching porn, my eyes kept going back to his crotch.
'Do you want to see my cock?' he asked suddenly and in one fluid motion lowered his pants and freed his hard member.
I was caught off-balance and was openly staring at it. It reminded me a bit of Tim's cock but larger. I was admiring the girth, the straight lines, the silky skin with the thick veins, the foreskin, the partially unveiled cock head, all entranced with a longing in my eyes.
'It's nice, isn't it?' he asked quietly.
'Yes...' I replied without thinking.
'You can touch it if you want.' he continued with the same quiet tone and a hind of a smile on his face. 'Go on, don't be shy.' he urged me when he saw I wasn't moving. 'I know you want to. I could see you staring at Tim's crotch earlier...'
At the mention of Tim's name I looked at him sharply, my mind slightly overtaken with worry.
'Nothing wrong with it.' he told me reassuringly after he saw traces of panic on my face. 'In fact, perfectly normal. After all, it does feel great. And I am sure you really gonna enjoy it'.
With my worries somewhat dispelled by his words, I reached tentatively and wrapped my hand around his shaft. I heard him sigh and felt his prick grow larger. Within seconds he was rock solid. Kevin was right, I did like touching his cock. His strong, warm pole felt great inside my hand. I really liked the feeling. He started moving his hips up and down slowly, his cockhead coming rhythmically in and out of his foreskin. He carefully took my wrist in his hand and started moving my arm up and down on his cock. I got the hint and took over the jerking off. The entire thing was just amazing. I was dreaming of this for so long that it all felt slightly surreal.
And when I was getting a grip on all this he asked in a quiet voice: 'Would you like to taste it?'
Seeing my inaction he added quickly: 'No one will ever know anything. It all stays between us. And I promise you, you really gonna like it. It tastes and feels amazing. Trust me, you will love it.'
It was as if he was inside my head, reassuring me, eradicating all my fears and insecurities to leave me only with pure desire. And just like that, I bent my head in one fluid movement and took his cockhead in my open mouth.
Once again he was dead right. It tasted great and it felt amazing inside my mouth. I took my time savouring it and exploring the new textures and flavours with my tongue when he got impatient, put his hands on my head and started pushing downwards firmly. I let my head relax and opened my mouth as wide as I could to accommodate as much of his cock as possible. Two thirds down I started gagging manically. He let me up for a few seconds to catch my breath and then started pushing back down.
This time he timed his pushing based on my breath. At one point he took one of his hands off my head, reached over his side and started stroking my ass and rubbing my ass crack. I was quite surprised when he first did it and didn't know how to react. Just as I realised I quite enjoyed his hand on my bum, I felt him tense. His cock expanded inside my mouth and he started shooting wave after wave of sperm directly inside my stomach. Before finishing he pulled his cock to the tip of my open lips and filled my mouth with the last bit of his cum. Once all finished he relaxed on the couch with a grunt. His cock, now soft and limb, slipped out.
'It tastes great, doesn't it?' he half asked half stated grinning at me.
'Yes...' I mumbled a bit embarrassed with my mouth full of spunk.
'That's your reward for all your great and hard work.' he told me smiling mischievously, 'Savour it and enjoy it. You've more than earned it.'
I felt oddly proud and embarrassed at his remark. I kept his cum in my mouth a few good minutes, enjoying the taste and texture before swallowing it. After a bit I realised he was staring at me with a smile on his face.
'So, was I right?' he asked me when I looked at him enquiringly.
'About what?' I asked back.
'Did you enjoy it as much as I did? Did you have fun?' he asked looking at my face intently, observing my reaction.
'Yes...' I replied shyly turning once again red.
'Great!' he exclaimed heartily 'I was kind of hoping you would. Tonight, when Tim's asleep, come over to my room. I have some more stuff in mind you are going to enjoy.'
At night, as soon as Tim fell asleep, I crept out of the room and with a stomach full of butterflies I headed towards Kevin's room. The room was at the other side of the house and with their mum staying at their grandma's, Fen away and Tim fast asleep, we had all the privacy in the world. When I reached the room I stopped for a few moments to compose myself. I was scared and excited at the same time. My heart was racing and my cock was throbbing. When a bit calmer, I knocked on the door. Kevin told me to enter.
The room was softly lit. Kevin was standing by the bed in his boxers with a raging hard on creating a tent at the front. The memory of his cock in my mouth was still fresh and vivid in my mind, and I craved for more.
'Take off your clothes,' he said as I approached him shyly and headed to the other side of the room. 'All of them' he added.
It wasn't a question or a request, it was more like a command, and as such I instantly felt the impulse to comply. Kevin so far had always asked for my opinion or made requests regarding everything we were doing. And yet when he issued the order, I felt excitement. Oddly, it felt strange but somehow appropriate. By the time I was naked he was standing in front of me with a bundle of clothes in his arms.
'Dress up' he commanded while handing me the clothes.
As I was picking up the bundle I realised it was all girl clothes. I've stared at it for a few seconds, confused. And then it dawned on me, he wanted me to dress up as a girl!
'Seriously?!' I exclaimed incredulous.
'Yea! Fen's stuff should fit you alright, plus she has a really good taste.' he replied excited and winked at me, 'It's gonna be real fun, trust me! You will love it!'
I stared at him still clutching the bundle, disbelief evident throughout my face.
'Oh, go on!' he urged me, 'At least try it. And if you don't like it, we'll stop. I promise.'.
Still unconvinced I started dressing up. First came a skimpy pink, laced thong. I was quite surprised that it actually managed to hold my now semi-limp cock and balls. I next put on a pair of white & pink, striped, holdup stockings and a blue mini skirt. After fumbling with the pink, laced bra, unable to hook it, Kev came around and did it himself. When finally I had the tight pink t-shirt on, he took me by the hand and sat me on the couch. He pulled a long black straight wig from a drawer and put it on my head.
He then grabbed a makeup kit from the dresser, squatted in front of me and started making my face up. He did my eyes, my cheeks and lips. When finished, he looked at me for a few seconds, smiled and leaned over and kissed me. I was happily surprised at how sensual my first kiss with a man was. His tongue was fleetingly exploring my mouth while playing with mine and I couldn't help but feel wanted and desired. I felt my cock stirring inside my panties.
Suddenly, all too soon, he broke away from the kiss, got up and told me to go and see how I look at the mirror. When I saw my reflection I was quite shocked at how different I looked. I kept staring, trying to figure out how I felt about all this. The clothes felt amazingly good on me. The wig and makeup felt a bit odd but they did made me look feminine.
Lost in thought, I heard Kev calling me to go to him. He was sitting naked on the bed, stroking his hard cock, looking at me with a lustful smile on his face. I quickly climbed on the bed, bent over and started sucking. After a while he put his hand on my head and just like before he started fucking my mouth. My whole attention was on the task at hand, trying not to choke. After some time, I felt his hand reaching under my skirt, stroking my bare ass. He moved my thong on the side and started rubbing my ass crack. The moment his finger touched my hole, I tensed. Shivers run through my entire body and I moaned with pleasure. I just couldn't believe how good it felt. My cock was hard instantly.
'You like it, eh?' he asked teasingly while rubbing and teasing my tight hole with the tip of his finger.
With my mouth full of cock I could only moan my agreement.
He was already playing with my ass and fucking my mouth for quite some time when suddenly he pulled his cock out, got up and went behind me. He spread my ass with his hands and when I thought it couldn't get any better I felt his tongue touching my hole. I started moaning and groaning uncontrollably while he happily ate my ass, licking and sucking at my hole. After a while he liberally applied lube on my ass, he rubbed it on my crack and slowly forced a finger inside my hole. My entire body tensed, all my muscles stiffened.
'Relax,' he said with his finger inside me, 'don't push out, keep it in.'
I did my best to accommodate him and as he felt my muscles relaxing around his finger, he pushed a second one in. He started massaging me from inside with fluid circular movements, widening my entry point. All I could feel was discomfort. After a while he took his fingers out, grabbed me by my waist, lined up his cock to my hole and started pushing. Once his cockhead was past my sphincter I whimpered. The pain was immense. It felt like I was being split in two. I instinctively tried to pull away but his hands on my waist kept me firmly pinned down.
'Don't move,' he commanded firmly 'it's gonna feel better in a minute.'
He leaned over and put a small bottle under my nose telling me to sniff deeply. With tears in my eyes, I inhaled as deep as I could and the pain faded slowly. My head started buzzing, my body relaxed and his cock started feeling nice inside me. He began pushing gradually in and out of me, with every push going deeper inside my ass. And with every push I was liking it more and more until I started pushing back against him.
'And how does it feel now little girl?' he asked with a laugh and in a single motion he rammed his entire prick inside me.
'Good!' I gasped as he started pounding my ass.
He was fucking me hard and fast, slamming his thighs noisily on me. Now and again he would slap my bum, telling me what a great ass I have and how he loved fucking me. And all the while I was lost in a pleasant haze, with my entire awareness focused on my ass. The fuck was really intense and the pleasure I was experiencing enormous. At times, Kev would abruptly slow down, pull his entire cock out, pour lube in my hole and shove it back inside me, resuming his powerful thrusts. Every so often, when feeling my entire body gradually stiffening he would tell me to inhale deeply from the bottle I was still holding - called poppers as I would later find out.
I sniffed deeply as instructed and every single time, within seconds, my sphincter relaxed loosening up my asshole, my anus sensitivity increased dramatically and I would spread my ass as wide as I could to accommodate as much of his cock as possible. I greedily pushed backwards meeting his thrusts, the impact jolting my entire body. I moaned and groaned uncontrollably. I just couldn't have enough of cock. In those first moments my entire universe consisted of Kevin's cock inside me. It all somehow felt right, exactly as it should be.
After what felt to me like ages, my body tensed up, stiffened, and suddenly I started squirting wave after wave of hot sperm. My orgasm was proving to be a long one. I was spasmodically shooting thick ropes of cum in sudden bursts. With every jerk, my sphincter was contracting tightly around Kev's cock and I could hear him gasping with each contraction.
'I can't believe you just had an orgasm just by being fucked!' he exclaimed between gasps, traces of surprise and disbelief evident in his voice.
I could only moan my reply as I kept squirting cum all over the bed in halting motions. Kev hadn't stopped fucking me, not even for a moment. He kept ramming my ass with the same punishing and relentless pace as in the beginning. When my balls were finally void of sperm, my body started cooling down. Within seconds my ass started feeling sore. Pain and discomfort radiated from my anus. I instinctively tried to pull away but once again he kept me still, his strong arms holding me in place by the waist.
'Where are you going baby girl? We are not finished yet!' he exclaimed as he kept pumping me.
The pain was growing and when he heard me whimper, in the verge of crying, he told me to inhale deeply from the poppers bottle and keep breathing it in until I actually felt good. I did as I was instructed and was quite surprised when on the third inhalation all the pain and discomfort were completely gone. I was even more surprised when on the fifth breathing I started enjoying being fucked again. Once more, I started pushing steadily backwards meeting Kev's thrusts.
'That's my girl!' he appraised me enthusiastically, 'Show me how much you like my cock! Show me how much you love being fucked!'
A sudden determination gripped me to prove myself and make him proud. I started pounding my ass against his cock with an alarming speed. Eventually he stood completely still, happy to let me impale my ass on his shaft. I kept going at it like crazy, slamming my ass noisily on his thighs. Then all of a sudden, he grabbed me by the waist, and with a really loud grunt he pulled me forcefully backwards while ramming his entire prick inside me. I gasped as I felt my gut filling up with his warm sperm. He was breeding me in intense bursts, shooting wave after wave of cum inside me. And when I thought my gut could hold no more of his man juice, he collapsed on top of me.
'That was fucking amazing, baby girl!' he whispered close to my ear. 'Your ass feels so good... so tight... so round and firm...'.
Strangely I quite liked being called 'baby girl', it felt appropriate. And I loved all the complements regarding my ass, they made me feel special and sexy as I've never felt before. As I was basking in Kevin's praise, he started licking my ear. Shivers run down my spine and I was again painfully aware of my hard on. His semi soft cock slipped out of my asshole along with a warm stream of cum. Finally he rolled off my back on the bed. He lay on his side facing me, looking directly into my eyes.
'I told you you'll love every bit of it, didn't I?' he said with a grin on his face.
I nodded shyly. He leaned closer and started kissing me passionately.
When I got up from the bed I received my first shock. Kevin had savaged my ass. I could barely stand, let alone walk. With the effects of the poppers gone and my body cold, the pain from the abuse of my ass came back with vengeance. I was convinced I hurt myself. When I voiced my concerns and complaints to Kev, he laughed, winked at me and told me that's the price for loving cock and sooner or later I'll get used to it!
When I was changing back to my clothes, Kev told me to keep the thong on as from then on I would wear only girly underwear. I looked at him incredulously but nonetheless did as I was told. After helping me clean up my face, he deep kissed me for a few good minutes, and with light squeeze on my butt, he bade me goodnight. Still horny and full of conflicting emotions, I crept into Tim's room and went to bed while trying to sort out in my head the events of the night.
The next day I woke up with my ass aching dully and my cock rock hard. As I was remembering the previous night I started feeling guilty and ashamed for enjoying the entire thing so much. And then I got my second shock. Even though steeped in guilt and shame, the more I was thinking of everything the hornier I was becoming. With my thong a pleasant reminder pressing against my aching hole, I longed for Kevin to take me again.
It surprised me how fast I came to accept and embrace my sexual role. How things that I've never even considered before in my life felt so sexy and natural to me.
I was seeing Kevin almost every other day and I couldn't have enough of him. Even though my mannerism was never particularly effeminate, the way he treated me always made me feel like a girl when we were together. He changed my name from George to Ginna and soon after started referring to me as his girlfriend. I was with Kevin for nearly two years and during this time I learned how to really appreciate cock. I was truly happy but it all came to an end quite suddenly when he had to move to the other side of the country for college.
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with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/crossdressing/becoming-ginna.aspx">Becoming Ginna</a>